1-(4-nitrophenyl)-1H-1,2,3-triazole-4-carboxylic acid | 4600-06-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-nitrophenyl)-1H-1,2,3-triazole-4-carboxylic acid
• 英文别名: 1-(4-nitrophenyl)triazole-4-carboxylic acid
• CAS: 4600-06-0
• 化学式: C₉H₆N₄O₄
• mdl: MFCD10696382
• 分子量: 234.171
• InChiKey: IKTCQCIOGLPNKA-UHFFFAOYSA-N

物化性质

• 熔点：
  202 °C
• 沸点：
  527.1±56.0 °C(Predicted)
• 密度：
  1.66±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(4-nitrophenyl)-1H-1,2,3-triazole-4-carboxylic acid 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 4-(decyloxy)phenyl 1-(4-nitrophenyl)-1H-1,2,3-triazole-4-carboxylate
  参考文献：
  名称：

  Synthesis and mesomorphic properties of novel [1,2,3]-triazole mesogenic based compounds

  摘要：

  A series of five-membered heterocyclic 1,2,3-triazole derivatives with different substituents in N1 position was synthesized. The heterocyclic moiety was connected through an ester function to a p-decyloxyphenyl or p-decyloxybiphenyl tails Polarized microscopy studies, X-ray scattering and differential scanning calorimetry (DSC) analysis revealed that the target compounds exhibit enantiotropic liquid crystalline properties. Their mesomorphic behavior is closely related to the nature of the substituent X present in N1 position of the heterocycle. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2012.09.020
• 作为产物：
  描述：

  1-(4-硝基苯基)-1H-1,2,3-三唑-4-甲醇 在 potassium permanganate 、 sodium carbonate 作用下， 以 乙腈 为溶剂， 反应 8.0h， 生成 1-(4-nitrophenyl)-1H-1,2,3-triazole-4-carboxylic acid
  参考文献：
  名称：

  炔丙醇一锅法合成1-单取代1,2,3-三唑

  摘要：

  实现了由炔丙醇和各种芳基叠氮化物一锅法合成 1-单取代-1,2,3-三唑。这种简单的方法通过三步一锅法以良好到极好的收率提供了对各种 1-单取代 1,2,3-三唑衍生物的简洁有效的访问。

  DOI：

  10.1055/s-0036-1589157

文献信息

• Synthesis, Characterization, and Biological Evaluation of New Derivatives Targeting MbtI as Antitubercular Agents
  作者：Matteo Mori、Giovanni Stelitano、Laurent R. Chiarelli、Giulia Cazzaniga、Arianna Gelain、Daniela Barlocco、Elena Pini、Fiorella Meneghetti、Stefania Villa

  DOI：10.3390/ph14020155

  日期：——

  with this class of compounds. The structure-activity relationships (SAR) here discussed evidenced the importance of the furan as part of the pharmacophore and led to the preparation of six new compounds (IV–IX), which gave us the opportunity to examine a hitherto unexplored position of the phenyl ring. Among them emerged 5-(3-cyano-5-(trifluoromethyl)phenyl)furan-2-carboxylic acid (IV), endowed with comparable

  结核病（TB）每年导致数百万人死亡，是全球最危险的传染病之一。由于结核分枝杆菌(Mtb) 的几种致病菌株已经对大多数现有的抗结核药物产生了耐药性，因此迫切需要新的治疗选择。开发新型抗结核药物的一个有吸引力的目标是水杨酸合酶 MbtI，它是分枝杆菌铁载体生化机制的必需酶，而人类细胞中不存在这种酶。 I和II是迄今为止鉴定出的两种最有效的 MbtI 抑制剂，其一组类似物经过合成、表征和测试，以阐明此类化合物实现有效 MbtI 抑制和有效抗结核活性的结构要求。这里讨论的构效关系 (SAR) 证明了呋喃作为药效基团一部分的重要性，并导致了六种新化合物 ( IV – IX ) 的制备，这使我们有机会检查迄今为止尚未探索的苯基位置戒指。其中出现了5-(3-氰基-5-(三氟甲基)苯基)呋喃-2-羧酸( IV )，其具有与之前的先导化合物相当的抑制特性，但具有更好的抗结核活性，这是MbtI的关键问题抑制剂
• Synthesis and comparative study on phase transition behavior of triazole-cored liquid crystals armed with cholesterol and double or triple aromatic rings systems
  作者：Guan-Yeow Yeap、Subramanian Balamurugan、Murugesan Vijay Srinivasan、Palaninathan Kannan

  DOI：10.1039/c3nj00053b

  日期：——

  Two homologous series of optically active bent-shaped mesogens comprising a cholesterol unit as one of the side arms connected to a 1,2,3-triazole ring while the other arm of the triazole ring is connected to two- and three-ring aromatic systems with varying terminal chain lengths have been synthesized. The molecular structure, thermal and optical activities have been studied extensively in which the compounds from both series exhibit polymorphism ranging from chiral nematic (N*), chiral smectic A (SmA*), chiral smectic C (SmC*) and twist grain boundary (TGBC*) phases. A further comparison between the two series of target compounds has drawn a common remark of which the phase behavior is found to be dependent on the length of the terminal tail and number of aromatic rings in the mesogenic units.

  我们合成了两个同源系列的具有光学活性的弯曲状中间体，其中一个侧臂由胆固醇单元组成，与 1,2,3 三唑环相连，而三唑环的另一个侧臂则与具有不同末端链长度的二环和三环芳香系统相连。我们对这两个系列的化合物的分子结构、热学和光学活性进行了广泛研究，发现它们具有手性向列相 (N*)、手性 Smectic A 相 (SmA*)、手性 Smectic C 相 (SmC*) 和扭曲晶界相 (TGBC*) 等多态性。通过对这两个系列的目标化合物进行进一步比较，我们发现了一个共同点，即相行为取决于末端尾部的长度和中生单元中芳香环的数量。
• In vitro and in vivo biological evaluation of newly synthesized multi-target 20(R)-panaxadiol derivatives for treating Alzheimer's disease
  作者：Lei Pang、Jin Li、Zheng Liu、Yin-Sheng Quan、He Huan Sui、Yi Jia、Fener Chen、Jung Joon Lee、Peng Liu、Zhe-Shan Quan、Qing-Kun Shen、Hong-Yan Guo

  DOI：10.1016/j.ejmech.2022.114825

  日期：2022.12

  disaggregation. The effective permeability of compound 14a across the blood-brain barrier was 26.13 × 10−6 cm/s, indicating that it can provide adequate exposure in the central nervous system. Further, compound 14a improved learning, memory, and novel object recognition in mice, and in vivo toxicity experiments confirmed a good therapeutic safety range. Thus, compound 14a is a promising multifunctional lead

  进行了广泛的研究以发现一系列在 3-OH 位置具有各种取代基的新型 20( R )-人参二醇衍生物作为治疗阿尔茨海默氏病的无毒、脑渗透性、多靶点先导物。体外分析表明，带有苄基取代氨基甲酸酯的化合物（我们将其命名为化合物14a）表现出最有效的神经保护活性，EC 50为 13.17 μM。化合物14a的神经保护作用比多奈哌齐略强，比 20( R )-人参二醇强得多。7.5–120 μM 的化合物14a在各种细胞系中表现出低毒性。此外，复合14a表现出广泛的生物学活性，包括抑制细胞凋亡；诱导 tau 过度磷酸化；影响 β-淀粉样蛋白 (Aβ)、β-分泌酶、活性氧、肿瘤坏死因子-α、环氧合酶-2 和白细胞介素-1β 的产生；促进 Aβ 25-35分解。化合物14a穿过血脑屏障的有效渗透率为26.13×10 -6  cm/s，表明它可以在中枢神经系统中提供足够的暴露。此外，化合物14a改善了小鼠的学
• Synthesis, and evaluation of in vitro and in vivo anticancer activity of 14-substituted oridonin analogs: A novel and potent cell cycle arrest and apoptosis inducer through the p53-MDM2 pathway
  作者：Qing-Kun Shen、Hao Deng、Shi-Ben Wang、Yu-Shun Tian、Zhe-Shan Quan

  DOI：10.1016/j.ejmech.2019.04.005

  日期：2019.7

  A series of novel oridonin derivatives bearing various substituents on the 14-OH position were designed and synthesised. Their antitumour activity was evaluated in vitro against three human cancer cell lines (HCT116, BEL7402, and MCF7). Most tested derivatives showed improved anti-proliferative activity compared to the lead compound oridonin and the positive control drug 5-fluorouracil (5-Fu). Among them, compound C7 (IC50 = 0.16 mu M) exhibited the most potent anti-proliferative activity against HCT116 cells; it was about 43- and 155-fold more efficacious than that of oridonin (IC50 = 6.84 mu M) and 5-Fu (IC50 = 24.80 mu M) in HCT116 cancer cells. Interestingly, the IC50 value of compound C7 in L02 normal cells was 23.6-fold higher than that in HCT116 cells; it exhibited better selective anti-proliferative activity and specificity than oridonin and 5-Fu. Furthermore, compound C7 possibly induced cell cycle arrest and apoptosis by regulating the p53-MDM2 signalling pathway. Notably, C7 displayed more significant suppression of tumour growth than oridonin in colon tumour xenograft models where the tumour growth inhibition rate was 85.82%. Therefore, compound C7 could be a potential lead compound for the development of a novel antitumour agent. (C) 2019 Elsevier Masson SAS. All rights reserved.
• Dimroth, Chemische Berichte, 1902, vol. 35, p. 1031
  作者：Dimroth

  DOI：——

  日期：——